1,4-bis(dihydroxyphenyl)butane (desmethylnordihydroguaiaretic acid) is useful as an antioxidant, such as for food preservation purposes.
Nordihydroguaiaretic acid has been used as an antioxidant, but is expensive both to procure from natural sources such as the creosote bush Larrea divaricata, or Larrea tridentata, and to synthesize, requiring starting materials not readily available commercially, or a multiplicity of processing steps, such as those disclosed in U.S. Pat. Nos. 2,456,443; 2,644,822; 3,769,350; 3,843,728; and 3,906,004, as well as C. W. Perry, M. V. Kalnins and K. H. Deitcher, "Synthesis of Lignans, I. Nordihydroguaiaretic Acid," 37 J. Org. Chem., 4371 (1972).
In contrast to nordihydroguaiaretic acid, 1,4-bis(dihydroxyphenyl)butane and its analogs may be easily and inexpensively synthesized using readily available reagents such as 3,4-methoxybenzaldehyde, or other substituted benzaldehydes. The substituted benzaldehyde is converted to a substituted phenylpropanol, which is halogenated and converted to a novel grignard reagent, such as 3,4-dimethoxyphenylpropyl magnesium bromide. This grignard reagent may be reacted with carbonyl compounds to produce intermediates for 1,4-bis-(3,4-dihyroxyphenyl)butane synthesis and a number of other novel compositions.